Frontiers of Entrepreneurship Research, 1995

Frontiers of Entrepreneurship Research
1995 Edition

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    Mike Wright, University of Nottingham, UK
    Ken Robbie, University of Nottingham, UK
    Christine Ennew, University of Nottingham, UK


    In order to shed light on serial entrepreneurs and to extend our earlier study of venture capitalists, the authors conducted in-depth face-to-face interviews with entrepreneurs who have exited from their first venture and become involved in subsequent ones. The study's findings suggest that serial entrepreneurs fall broadly into two groups. The first group undertake a second venture primarily for defensive reasons, typically in the same sector and even the same firm. The second broad group act rather more opportunistically with the aim of achieving rapid growth of their ventures. This group can be divided into two sub-groups, 'group creators' and 'group developers'. Evidence from the study indicates greater continuity of relationships with bankers and professional advisers than with venture capitalists. Serial entrepreneurs considered that they now understood the workings of venture capitalists better, making them more aware and able to identify a compatible partner and to negotiate terms that suited them.


    Growing research effort has been devoted to serial or habitual entrepreneurs. Given that entrepreneurship may involve the purchase of an existing business as well as the formation of a new one (Cooper and Dunkelberg, 1986) the number of serial entrepreneurs may be quite large. These serial, second time, habitual or multiple entrepreneurs may provide important insights into the nature of entrepreneurship and raise questions concerning the relationship between entrepreneurship experience and venture performance (e.g. Starr and Bygrave, 1991). Entrepreneurs may become involved in several ventures simultaneously, or may exit their first one before embarking on one or more subsequent ones. Furthermore, some may be devoted to their ventures on a full basis while others may have only part time involvement and in some instances this involvement may be in the form of a business angel role (Harrison and Mason, 1992).

    The first section of the paper discusses the nature of serial entrepreneurship and provides an extension of the relatively limited existing literature by developing a typology of serial entrepreneurship based on a broad definition of entrepreneurship which includes both the foundation and acquisition of new ventures. The second section outlines the data sources and methodology used in this study, which involved in-depth face-to-face interviews with serial entrepreneurs. The third section presents the results of the interviews. The final section presents the conclusions and implications of the research.

    As indicated in the introduction, this paper takes a broad perspective on serial entrepreneurship and we identify a number of different forms which it may take (Wright, Robbie and Ennew, 1994). These different forms of serial entrepreneurship are shown in Table 1.

    Essentially the categories of second time entrepreneurship may be represented as; repeating entrepreneurial experience with the same enterprise - i.e. selling out from whatever form the initial venture took and then buying it, or part of it, back (a secondary MBO); repeating entrepreneurial experience by leading a new venture involving a company which already exists and which may (a pure management buy-in, MBI) or may not (a buy-in/buy-out, BIMBO) involve incumbent management in equity ownership; repeating the entrepreneurial experience with an entirely new company (a start-up).

    Repeating an entrepreneurial experience with an entirely new company is generally regarded as the classic case of serial entrepreneurship. Both US studies (eg Ronstadt, 1988) and UK studies (Birley and Westhead, 1994) have identified a high incidence of serial business founding. However, serial entrepreneurship may also entail re-establishing a relationship with previously owned company. Following the sale of the initial venture the entrepreneur may initially remain with the new parent following sale as her specific skills are key to the value of the venture but may subsequently effect a buy-out as either the acquisition fails to fit or the parent experiences major trading difficulties. Petty, Bygrave and Suhlman (1994) using US data find that entrepreneurs who sell their businesses to another group have a number of reservations, including a sense of loss within their lives. Hence entrepreneurs may seek to reestablish ownership to make good their sense of loss.

    Management buy-ins provide a further medium for serial entrepreneurship. Evidence indicates that well over a quarter of buy-in team leaders had previously owned a significant equity stake in a company in which they had been employed (Robbie and Wright 1995). Although such investments have many of the features of start-ups they generally involve lower risk than entirely new ventures. Typically, significant entrepreneurial input is required to turnround an enterprise subject to a buy-in, (Robbie and Wright 1995). Experienced entrepreneurs may be sought to complement inexperienced incumbent management, creating a BIMBO, in order to make a transaction feasible. Experienced entrepreneurs making minority and/or part-time investments as business angels may have a comparative advantage over formal venture capitalists in making helpful contributions in operational and strategic functional areas of an enterprise's activity, though there appear to be significant difficulties in the process of searching and matching investors with investments (Harrison and Mason, 1992).

    As the above discussion illustrates, serial entrepreneurship can and does take a variety of forms and is likely to involve a variety of different individuals. Considerable attention has been devoted to the identification of entrepreneurial typologies with a clear view emerging that entrepreneurs do not display homogeneous characteristics. A frequently recurring theme has been the existence of two main types of entrepreneurial individuals- the craftsman and the opportunist. Examination of the characteristics of the leading individuals in buy-out and buy-in transactions identifies similar features to those found in respect of entrepreneurs who start new ventures, with buy-in entrepreneurs generally having more proactive features than their counterparts in buy-outs (Robbie and Wright, 1995). Similarly, serial entrepreneurs may be expected to display heterogeneous characteristics.

    There is also evidence to suggest that the performance implications of serial entrepreneurship are surrounded by a degree of ambiguity. Stuart and Abetti (1990), find that the most significant influence on performance was the level of managerial experience in previous ventures. Studies which have specifically examined cases of serial entrepreneurship are less sanguine. Starr and Bygrave (1991) have pointed to the potential liabilities of earlier experience for subsequent ventures. Keeley and Turki (1992) emphasise the importance of examining repeat entrepreneurship in the context of industry life-cycles and the different scales of enterprise (and hence range of skills and finance required) which may be involved in successive ventures.

    Birley and Westhead (1994) found no evidence to suggest that new businesses established by habitual founders are particularly advantaged compared to their more inexperienced counterparts. Kolvereid and Bullvag (1993) examine differences between novice and experienced business founders where experienced entrepreneurs still own their original business. They are unable to identify performance differences between the two types of entrepreneur. However, Leleux and Muzyka (1993) point out that these results may be biased because of the exclusion of cases where the founder had exited from the initial venture in the definition of successful first ventures.

    In order to explore further the issues surrounding serial entrepreneurship, it is useful to consider not just the types and performance of serial entrepreneurs but also to examine the process surrounding the decision to get involved in a second or subsequent venture. In particular, the role of financing institutions may merit specific examination, not least because prior entrepreneurial success may be seen as an important indicator of future potential. Certainly, MacMillan, (1987) show that the most important criteria used by venture capitalists in screening investment proposals were entrepreneurial personality and experience, with lesser dependence being placed on market, product and strategy. However, Starr and Bygrave (1991) point out that previous venture experience may have both positive and negative features.

    The authors' earlier study of venture capitalists' approaches to serial entrepreneurs suggests that the extent to which venture capitalists use previously funded entrepreneurs is relatively low compared to the number of investments harvested (Wright, Robbie, Ennew, 1994). The study lends support to Starr and Bygrave's (1991) observation about the liabilities of experience. Although previous ownership experience is of some importance it is not of itself a critical factor, since indications are that venture capitalists will need to be satisfied that experienced entrepreneurs still have the motivation, ambition and managerial skills to succeed in a subsequent venture. These points may be especially true of entrepreneurs exiting from a management buy-out, who typically may have been reacting to the presentation of a one-off opportunity in the enterprise in which they find themselves.

    Interestingly, our earlier study also found that venture capitalists made extensive use of entrepreneurs previously funded by other venture capitalists. This behaviour raises potential adverse selection problems. Departing venture capitalist through having personal experience of the entrepreneur may make a different judgement from an incoming venture capitalist about the abilities of the entrepreneur to move from say a management buy-out to a management buy-in where different types of managerial and entrepreneurial skills are required.

    While original venture capitalists may be reluctant to fund an exiting entrepreneur in a subsequent venture, the entrepreneur may also be reluctant to join with the venture capitalist again. Entrepreneurs who sell their business may retain a formal management position with the new owners or decide to pursue some totally different activity not involving a venture capitalist or wish to pursue a venture but with an alternative financing structure. Entrepreneurs may be reluctant to remain with the same venture capitalist especially if there had previously been disagreements over the way the initial harvesting process was managed, disputes over equity ratchets or more fundamental problems in the personal relationship between the venture capitalist and the entrepreneur. Higher levels of personal wealth resulting from a successful sale of their first business may enable the second time entrepreneur to avoid the use of venture capital finance in the initial stages of a second venture. There may also have been a significant change in the relative bargaining powers of the entrepreneur and venture capitalist.

    The nature of continuing relationships with bankers and professional advisers also arises. In general, all enterprises need a bank relationship, not least to enable operational financial transactions to be carried out though in reality it may also involve a much wider set of activities. Evidence suggests major shortcomings in the relationships between banks and enterprises (Ennew and Binks, 1995) and might indicate that exit from a venture may provide an opportunity to forge a new banking relationship. However, this evidence also suggests that entrepreneurs may demonstrate considerable loyalty to a particular individual within the bank. Loyalty in the banking relationship may also be influenced by the absence of the kind of conflicts which arise in respect of venture capitalists who hold part of the firm's equity. Hence, in contrast to the position with regard to venture capitalists, serial entrepreneurs may be expected to be more likely to maintain a relationship with their banker.

    Hustedde and Pulver (1992), show that entrepreneurs who fail to seek advice were likely to be less successful in acquiring equity finance. Evidence does show that entrepreneurs select advisers who are already known to them but in a significant proportion of cases the adviser is selected after the venture capital partner is identified. When professional advisers were involved at an early stage, they usually had an important influence especially on identifying sources of venture capital (Murray and Wright, 1995). However, the approach of serial entrepreneurs to the use of professional advisers after their first ventures is ambiguous. On the one hand, experienced entrepreneurs may consider that they now have sufficient wealth and experience not to require the skills of professional advisers. Alternatively, signalling theory suggests that experienced entrepreneurs will both seek to employ first rate advisers (e.g. Big Six accounting firms) and by virtue of their experience be attractive clients for such firms.


    The study involved a series of in-depth interviews with thirteen entrepreneurs who have exited under conditions of success from their first venture and become involved in subsequent ones. However, as most second ventures were at a relatively early stage it has not been possible so far to ascertain whether these serial entrepreneurs were able to repeat their first time success. As there is no readily available list of serial entrepreneurs covering all the categories identified in Table 1, the entrepreneurs were selected partly from the CMBOR database, maintained by the authors and which covers the population of new and exiting buy-outs and buy-ins in the UK, and partly from venture capitalists and advisers who had experience of serial entrepreneurs. Of the seven entrepreneurs who had completed a buy-out first time around, three did so in their second ventures, three undertook a buy-in and one engaged in a start-up. The one entrepreneur who initially undertook a buy-in also used this vehicle to effect his second venture. The remaining five entrepreneurs had all started a venture at first with two each undertaking buy-ins and start-ups for their second ventures and the fifth involved in a hybrid buy-out/buy-in. The interviews were carried out in spring and early summer 1994 and lasted between one and two hours each. The interviews were conducted on the basis of a semi-structured questionnaire derived from issues raised in the existing literature and the earlier survey of venture capitalists. The questionnaire was initially piloted among academic researchers, venture capitalists, advisers and serial entrepreneurs.

    While the study involved only a small sample of serial entrepreneurs it contributes to the issues discussed in this paper in three principal ways. First, it gives insights as to the entrepreneurs' perspective on subsequent ventures which in turn provide comparisons with the views of venture capitalists. Second it highlights possible differences between types of serial entrepreneur and third it sheds further light on the relationships between entrepreneurs and their advisory teams.


    The types of the first and second ventures together with a summary of the motivations in each venture are shown in Table 2. The essence of the first and second ventures, together with the intermediate activities of the entrepreneurs are shown in Table 3. The principal results are presented in three sections. The first identifies types of serial entrepreneur based on their motivations and approaches to their various ventures. The second section analyses the processes involved in becoming a serial entrepreneur. The third section discusses the entrepreneurs' perceptions of the roles played by venture capitalists, banks and professional advisers in the first and subsequent ventures.

    Motivations and Characteristics

    The earlier discussion suggested the hypothesis that serial entrepreneurs may be expected to display heterogeneous motivations and characteristics. As noted in the previous section, the entrepreneurs surveyed had effected a successful exit from their first venture in that they had not been forced to exit because of poor performance and had all acquired some degree of capital gain on their initial investment. There are some indications from the case studies that monetary gain was of limited significance and where it had been a factor in the first venture it was less important in the second. Entrepreneurs in their second venture committed a significantly smaller proportion of their personal wealth than in their first. Although the sensitive nature of this issue makes precise estimates difficult, typically ten to twenty percent of an individual entrepreneur's net worth was invested. Entrepreneurs were clear that they did not wish to commit more than a small minority of their wealth but also recognised the importance of being committed to the deal. Although entrepreneurs personally were much less financially exposed than in their earlier venture, they were concerned as to the potential effects of venture failure on their personal reputation.

    Apart from those who started a business the second time around, there was little positive motivation for such a move, partly because of a desire to reduce risk exposure and partly because of the difficulty in obtaining funding for the size of start-up that these serial entrepreneurs were primarily interested in. In general, the desire for a challenge and/or in some way to develop an idea or business emerged as the strongest motivating factors, particularly in the second and subsequent ventures (Table 2).

    Although it was not possible to undertake formal cluster analysis, the results of our interviews suggest that serial entrepreneurs fall into two broad groups (Table 3). The first group undertake a second venture primarily for defensive reasons, typically in the same sector and even the same firm, often as a reflection of their loyalty to that firm. Essentially they can be seen as 'venture repeaters'. The second broad group act rather more opportunistically with the aim of achieving rapid growth of their ventures. This group can, however, be divided into two sub-groups, 'group creators' and 'group developers', being distinguished by the motivations and the methods used to develop their ventures. To some extent, these groups parallel the craftsman/opportunist distinction identified in other research on entrepreneurial types.

    Defensive Serial Entrepreneurs - Venture Repeaters

    These entrepreneurs tend to be reactive, effectively undertaking their second venture because there was little obvious alternative. Most entrepreneurs in this category are individuals whose initial venture was a buy-out; sometime after the buy-out was sold to another group, the entrepreneur buys it back. Such a purchase typically occurs when the company or its new owner begins to experience operational or financial problems. The entrepreneurs in exiting from their first venture may have remained with the company under its new owner, either as divisional head or as a main board member. This type of entrepreneur is less likely to have become involved in searching for other buy-in or start-up ventures during the period between exit from the first venture and embarking on the second. The entrepreneur may have a strong personal commitment to ensuring the survival of the business and be keen to rebuild and repair it after a period of what he considers to have been unsatisfactory ownership.

    Opportunist Serial Venturers

    This group of entrepreneurs have common features in that capital gain as well as the challenge of developing a business is frequently an important motivating factor. The first venture may have been undertaken for a mixture of motives including a desire for independence, wealth creation, or a desire to remain in employment. In the second venture the challenge and interest of creating and/or developing a new group was a common and major motivating factor. Unlike venture repeaters, entrepreneurs in this group are generally active between their first and second ventures in searching for a suitable opportunity. Moreover, unless there are special factors, these entrepreneurs are likely to undertake further ventures when they have exited from the second one. The two sub-groups can be distinguished as follows:

    Group Creators ('Serial Dealmakers')

    For this group of entrepreneurs, acquisitions as well as group development play an important role in developing their second and subsequent ventures. They tend to consider a number of intermediate ventures which may or may not involve investment and which may or may not be successful. Moreover, these entrepreneurs are also more likely to be involved in more than one venture at the same time.

    Group Developers ('Organic Serials')

    This group of serial entrepreneurs is more likely than the first to be motivated by the challenge of developing their second venture through organic growth, with considerably less emphasis on the role of acquisitions. In some cases the experience of serious difficulties following acquisitions made as part of the first venture may have a critical influence on the approach to growth made in the second deal. Intermediate activities are likely to involve managerial employment, including remaining with the initial venture for a period of time following the sale of equity.

    The Process of Becoming a Serial Entrepreneur

    Entrepreneurs may move directly from their first to their subsequent ventures. Alternatively, they may arrive at another investment rather more indirectly after a period of searching for an appropriate vehicle. The mechanisms by which the second venture is identified is an important part of understanding this process as well as the influence of the positive and negative aspects of the first venture experience. The more defensive venture repeaters either remained employed in the company until the second possibility for a buy-out presented itself, or they bought out a part of the larger enterprise from which they were exiting.

    The more opportunistic serial venturers were much more likely to engage in a search process which involved consideration of several alternative possibilities, with or without making an investment, before undertaking the second major venture. In a number of cases these intermediate investments were not successful but tended to be relatively minor ones. As noted above, organic serials are likely to be involved in managerial employment, including remaining with the initial venture for a period of time following the sale of equity; serial dealmakers tend to consider a number of intermediate ventures which may or may not involve investment and which may or may not be successful. There was a slightly greater tendency for the opportunists to undertake their second venture in a different market sector from the first. These cases involved those serial dealmakers who undertook a buy-in the second time around. Entrepreneurs starting-up a business in their second venture typically remained in the same market sector, although the actual products involved may be different.

    Experiences in the first venture had some influence on the manner in which the second venture was approached. Two particular aspects stand out. Entrepreneurs generally reported good relations with venture capitalists in the first venture. However, considerable emphasis was placed on the positive benefits gained from the first venture in respect of understanding how financing institutions operated and a greater feeling of confidence in knowing how to negotiate with them. This experience was particularly seen as being useful in respect of the timing of exit. The second most important area concerned the need to give considerable attention to the running of the business. There was a clear appreciation of the need to maintain a focus on the venture's strategic direction. Those entrepreneurs who had made acquisitions as a means of trying to grow the first venture expressed the need for particular care in such transactions and for the most part regretted having pursued this route. Other benefits from the first venture concerned general experience of running one's own business, the need to obtain a significant equity stake in the business in order to moderate institutional pressures for exit and the financial gain. Moreover, having built a reputation as a successful entrepreneur the first time around, the individuals involved were reluctant to do anything which undermines their own standing amongst relevant business and financial communities.

    Roles of Professional Advisers and Financiers

    Serial entrepreneurs make extensive use of professional advisers and financiers, but their roles and the players involved may change substantially between the first and second ventures. Entrepreneurs who are qualified accountants or lawyers tended to consider themselves better able to undertake more of the detailed work in completing a deal than was the case for those with a general management background. By far the most important change occurs in respect of venture capitalists, whilst relationships with bankers are generally marked by continuity unless very specific influences are involved. The changes affecting professional advisers fall between these two extremes.

    Changes in the use made of venture capitalists are particularly interesting in that they support the results of our earlier study of venture capitalists (Wright, Robbie and Ennew, 1994) which showed relatively low levels of involvement in new ventures of investees who had exited, but that venture capitalists did make use of entrepreneurs who had exited from other venture capitalists portfolios. However in nearly all cases, occasional social contact was maintained with the venture capitalist following exit, whether or not a subsequent investment was made.

    There was relatively little evidence from the cases of venture capitalists being proactive in offering potential deals to the entrepreneurs. The cases where a venture capitalist was not used the second time around essentially involved ventures which were substantially smaller than the first one. Here the combination of personal wealth obtained on exit from the first venture together with bank financing obviated the need for venture capital. Some entrepreneurs also perceived that the market focus and the level of activity of the venture capitalist who had backed them the first time around had changed since the original deal so that they were unlikely to be in a position to invest a second time. To some extent this shift between first and second ventures also reflected the well-known reluctance on the part of some entrepreneurs to relinquish equity and allow a degree of control by an outside party. To do so may be necessary the first time around but can be avoided once a degree of personal wealth has been achieved. In two cases the entrepreneurs had attempted to attract a venture capitalist, in one case the lead investor from the first venture, but had been turned down as the transactions were considered not to offer the prospects of sufficient returns to outweigh the risks involved.

    Where there was a change of venture capitalist between the first and second venture this primarily occurred because the size of deal involved was much larger or because the second venture was of a markedly different type from the first. In only two cases was the same initial lead venture capitalist retained as deal leader in the second venture, although in a third case a member of the syndicate in the first emerged as arranger in the second venture. Entrepreneurs were highly conscious that success in the first venture gave them a track record which was an important and verifiable attribute in helping to negotiate the best terms from a wider choice of venture capitalists. Entrepreneurs in selecting financial support for the second venture were also more aware of the venture capitalists' exit time horizons.

    Those serial entrepreneurs making use of venture capital for the second venture, but not in the first, were generally involved in start-ups. The first venture tended to be small so that it was possible to fund it from personal sources and modest bank financing. The amount of funds involved would typically be below the minimum criteria set by most venture capitalists. Venture capital was obtained in the second start-up primarily because the size of the venture was much greater. Reductions in the degree of risk for the venture capitalist between the first and second venture were considered to be important in being able to introduce an outside funder in the second deal. Whilst there was some expression of the view that venture capitalists had exerted too much influence the first time around, the influence of the venture capitalist in monitoring their investments was generally viewed as highly positive. Indeed, there were indications that venture capitalists, where they were present in the second venture, had a closer monitoring role than in the first. There was however concern in some cases over the background of venture capital firm representative whose length and depth of experience may have been much shallower than that of the successful entrepreneur. Some entrepreneurs exerted considerable perseverance in identifying a venture capitalist the second time around. Interestingly, the 'serial dealmakers' appeared to be rather more critical of the role and involvement of their venture capitalist when compared to either the organic serial or the venture repeater. This may reflect a greater resistance to interference and a greater desire for autonomy among the former group.

    Without exception, the serial entrepreneurs interviewed considered their relationships with bankers in the first venture to be very satisfactory. The basis for such a high level of satisfaction was typically attributed to very supportive individuals within the banks, although it may also reflect the tendency of the banks to adopt a rather more passive role when compared with the venture capitalist. Often the same individual was involved over a considerable period of time, with the relationship even pre-dating the initial venture. Consequently, entrepreneurs generally sought to retain the same bank for the second venture. This support was notably forthcoming in ventures which involved a second buy-out where the enterprise had deteriorated significantly following exit from the first transaction. The entrepreneurs in the cases involved accepted covenants on their borrowings which had been absent the first time around.

    Bankers tended not to be retained if the bank was no longer in the relevant market segment, where the entrepreneur had changed regions, and where frequent internal movements of staff in the bank effectively prevented the continuation of the personal banking relationship. As the second venture developed, however, it was not unusual for entrepreneurs to diversify their banking arrangements, particularly when acquisitions were being made. Such actions may or may not meet with the approval of the original bank. Key reasons for remaining with the same firms of professional advisers surrounded the credibility they gave to the entrepreneur in negotiating the second venture, both in terms of the provision of testimonials as well as the direct advice they offered. Where the same professional adviser was not retained, this was either because the serial entrepreneur felt that they now had enough experience to handle matters themselves or because a casual contact introduced the opportunity to become involved with another adviser.


    The results of this study have implications for both academics and practitioners. The face-to-face interviews indicated that venture capitalists may need to be aware that serial entrepreneurs are not a homogeneous group. As such it appears too simplistic to argue that serial entrepreneurs are 'more' entrepreneurial than novices. Although there were differences between individuals, capital gain appeared generally to be less important as a motivating factor the second time around with a desire to develop an idea or business within less exposure to financial risk being more important. Personal commitment to the second venture's success was high. Two principal types seem to be emerging. The first group undertake a second venture primarily for defensive reasons, especially in the form of a management buy-out. Essentially they can be seen as 'venture repeaters'. The second broad group can be divided into two sub-groups, 'group creators' (serial dealmakers) and 'group developers' (organic serials), There was a slightly greater tendency for the serial dealmakers to undertake their second venture in a different market sector from the first, especially if they were undertaking a buy-in the second time around. Entrepreneurs starting-up a business in their second venture typically remained in the same broad market sector. Quantitative academic research is warranted to explore further these tentative clusters.

    Evidence from the interviews indicated greater continuity of relationships with bankers and professional advisers than with venture capitalists. Part of the reasons for changing venture capitalist related to the smaller nature of subsequent ventures and greater personal wealth. Whilst relationships with venture capitalist had generally been good in the first venture, serial entrepreneurs considered that they now understood the workings of venture capitalists better, making them more aware and able to identify a compatible partner and to negotiate terms that suited them, especially in respect of exit horizons.

    For practitioners, the findings lend support to the results of our earlier survey of venture capitalists. Indications that serial entrepreneurs are not homogeneous suggests that practitioners need to match entrepreneurial types to particular situations. Hence, only some serial entrepreneurs appear suited to a context where growth is best achieved through a series of acquisitions, while others are more suited to achieving organic growth. While venture repeaters may be attempting to emulate their earlier success this may be problematical where conditions have changed significantly since the first buy-out. The findings also emphasise the importance of continuing relationships with bankers and the importance of the link between the entrepreneur and a particular individual in the bank. Similarly, the reasons for remaining with the same professional adviser, particular where the adviser is a major firm, are consistent with signalling theory.


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